


Jail and Bail

by AthenaScarlet



Category: Once Upon a Time (TV)
Genre: Alternate Universe, Angst, F/M, Fluff
Language: English
Status: Completed
Published: 2014-12-09
Updated: 2015-01-20
Packaged: 2018-02-28 19:46:11
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 13,415
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2744819
Author URL: https://archiveofourown.org/users/AthenaScarlet/pseuds/AthenaScarlet
Summary: <blockquote class="userstuff">
              <p>After getting arrested, Killian Jones needed someone to bail him out of jail. He just didn't expect his bail bondsman to be an attractive woman. Now he has to deal with the humiliation of being an accidental criminal and the rejection from a woman who has stolen his heart.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This is a Captain Swan AU fic based off a generic prompt I found on tumblr in which character A is bailed out of jail by character B. It should only be about seven or eight chapters when it's all finished so enjoy the ride! Also, some of you may find Killian a little OOC, but I tried to go with a more Lt. Jones angle than a Captain Hook one. Hope you guys like it!

He had called Liam three hours ago and yet still had no clue when he was getting out of this hell called a holding cell in Manhattan.

Frankly, he had no idea why he was even here in the first place. It was all a simple misunderstanding and he was more than willing to fix the mistake. But the cops who conveniently were standing right there when he accidentally walked out of the store with merchandise he forgot to pay for didn’t feel like his explanation was good enough. In fact, when they ran his ID through the system, they told him they had no choice but to lock him up and set bail because he had an outstanding warrant for his arrest.

None of this was making any sense. Killian was a good guy with a good record. He would never be one to break the law. He was all about good form and having an outstanding warrant was definitely not good form. And yet here he was in a holding cell with a bunch of true criminals.

“It’s all just a misunderstanding, I’m sure,” he told some guy named Jimmy.

“That’s the way it is for all of us,” Jimmy replied, taking a bite out of the bologna sandwich that Killian had refused to eat.

“No, I mean it. The cops just wouldn’t let me explain.”

“They never do.”

Killian was getting nowhere with that conversation and realized it was probably in his best interest to just shut up and keep his head down. That’s when he heard whistling coming from some of the guys standing near the cell’s bars up front.

“Look who’s here, boys!”

“You are quite the fine specimen in that dress, Swan.”

“Coming to pick me up tonight, princess?”

“Not tonight, Sal,” came a woman’s voice from the other side of the bars.

Killian looked up and saw the beautiful voice matched a beautiful woman with blonde hair, a black leather dress and long legs accentuated with tall platform high-heeled shoes. In one hand she was holding on to a man who had his wrists cuffed and in the other were some manila folders.

“Is this your idea of a hot date, Swan?” one of Killian’s fellow arrestees asked.

He watched her unlock the cuffs under the watchful eye of the cop standing next to her before shoving the man into the holding cell.

“I usually prefer men who can actually pay me back,” she said. “So no, it was not a hot date.”

A few of the men in the cell turned to look at their new roommate, staring him down. “You stiffed Swan?” one of them asked. Another made a “tsk, tsk” noise before explaining, “You really shouldn’t have done that.”

“That’s enough, boys,” the woman said. “Thanks for the concern, but I can handle myself.” Killian watched her pull out the manila envelopes and look at the names on the tabs. “So I’m taking Jimmy Russo, Mikey Zino and Killian Jones with me.”

Killian let out a deep breath, thankful that he was finally getting out of this place. Liam said he would find a bail bondsman after Killian decided to be stubborn, as his brother said, and handle the payment on his own. But he was a little shocked that it was a very attractive woman getting him out of here.

He followed the woman along with her charges down the hall to what he assumed was processing where he would hopefully be reunited with his wallet and phone before getting out of this awful place. But he was a little distracted by the gorgeous blonde holding his freedom in her hands -- literally -- to focus on his belongings. He watched as she looked over the folder for Jimmy, giving him a piece of paper along with a smile before he went to the counter to pick up his things. Then the man he assumed was Mikey sat down with her, whispering quietly as she filled out some paperwork to hand to him. As he left, she made sure to remind him that his boss had a bill due next week. Mikey nodded.

“Don’t worry, Swan. We’ll take care of you.”

She closed that folder and opened the last one in front of her. After scanning the page, she looked up, her green eyes standing out among the dreariness of the bleak cinder block walls around her.

“Killian?”

He nodded and she motioned with her hand to have him sit down across from her.

“So I talked to Liam earlier. He said he was your brother?”

“Aye,” Killian responded nervously.

She smiled. “I know this is a little strange seeing that it’s your first offense, but don’t be nervous,” she said. “Besides, this is nothing. It was just the outstanding warrant that made the cops a bit jumpy, and you’ll probably have that dismissed with a simple fine or something.” She looked back to her file and started turning pages. “So you got arrested for shoplifting?”

“I was picking up a gift for my friend’s son and totally forgot I had put it in my pocket,” he explained. “And of course, I accidentally walked out with it right as the cops were coming by.”

Swan started scanning the pages. “It was a …”

“Captain Hook action figure from the Disney Store.”

She laughed. “Well, that’s a first for me,” she said, smiling at him to try and ease his embarrassment. “Apparently, the store manager doesn’t want to file charges, so you don’t have to worry about that.”

Killian exhaled as if a weight was lifted off his shoulders. “Thank you.”

“So the only outstanding issue is this piracy charge.”

Killian looked up, startled at the news. “The what now?”

“Piracy charge,” she explained. “It looks like you illegally downloaded a song back in 2002 and the recording industry wanted to make an example of you.”

“Seriously?” he asked incredulously. “I thought all those letters about that were junk mail.”

“Don’t worry,” she said, writing some things down on a piece of paper. “I’ve seen people get away with much worse.”

Killian scoffed. “I got arrested for shoplifting and downloading music. I think I’m probably the most pathetic ‘criminal’ you’ve ever dealt with.”

“Not true,” she said, looking up at him with those green eyes again. “Last week, I had to bail out a grandma who was charged with aggravated assault.”

“Doesn’t aggravated assault involve a weapon or something?” he asked. “That seems less pathetic than an action figure.”

“She broke her neighbor’s leg by running over him with her motorized scooter. So maybe it was the neighbor that was the pathetic one in that case.” She went back to writing some more things down. “Although I do have to ask why you downloaded ‘I Have Nothing’ by Whitney Houston.”

Killian once again put his head down in embarrassment. “It was for a girl,” he muttered.

(Regina made out with him in college once -- once! -- and then rebuffed his advances. Why he thought a mix CD with Whitney Houston would change her mind is beyond him. It must’ve seemed logical to the 19-year-old version of himself.)

“So, paperwork,” Swan said. “Here’s your receipt for the bail. You owe me that plus 10 percent interest.”

“10 percent?”

“Yea, but that’s just until the end of the month. It goes up after that, so I would suggest you pay it as soon as you can.” She circled an address and phone number at the top of the page. “That’s me: Emma Swan,” she said, smiling at him before closing the folder in front of her. “Do you have any questions?”

Killian just shook his head, staring at the name on the page. Emma Swan was a beautiful name for a beautiful woman -- who was going to take his beautiful money.

“Thanks,” he said quietly.

Emma leaned down and put her hand on his shoulder. “Don’t worry, Jones,” she said. “It won’t be long before this is just a funny story you tell at cocktail parties.”

He stood up and folded the paper, sticking it in the inside pocket of his suit jacket. “Yea, sure,” he replied before sticking his hand out to shake hers.

She took his hand and smiled at him. “Don’t take this personally, but I do hope I never see you again,” she said. “You’re too good looking to be hanging out in a place like this.”

With that, she grabbed her folders and turned on her high-heeled shoes to walk out the door. Killian took a deep breath to steady himself and went over to pick up his belongings. He definitely wasn’t going to forget about this stupid turn of events anytime soon -- and he highly doubted he would forget about the woman who bailed him out either.


	2. Chapter 2

Killian watched as Neal played in the corner with his new Captain Hook toy. He had decided to go to a different Disney store to pick up the gift for the five-year-old’s birthday instead of dealing with the indignity of going to a place where he accidentally shoplifted something. And since David and Mary Margaret had put together a pirate-themed party, there really was no other option -- or at least that’s what Killian figured. He was single and didn’t have any kids so toys for other people’s children weren’t really his strong suit.

Actually paying for them wasn’t really a strong suit either. Killian was quite grateful when his brother and David offered him a job at their ad agency after being laid off almost a year ago. But losing his job had taken a toll on Killian’s wallet and he definitely didn’t have enough built up to pay for bail. Plus, he had repeatedly told Liam not to give him the money. He got himself into this stupid mess, he could get himself out.

Even so, Liam had helped get him out of trouble, but his solution just caused more problems. Well, actually just one problem: Emma Swan. Maybe it was just because he was in jail with some ugly guys or desperate for a friendly face, but Killian couldn’t forget her. He kept thinking about her hair or her dress or, more often than any of those combined, her green eyes staring at him.

Killian was a creative type, especially when it came to sketching at his ad agency job, but he was having a hard time trying to creatively see Emma again. The only idea he had was to just go over to her office and pay his bail in person. But with only a boring plan and a looming deadline -- seriously, 10% interest? -- he had no choice.

“I hope you’re having fun,” Mary Margaret said as she walked up next to him with a tray of pirate-themed cupcakes in her hand.

“I am,” he replied earnestly, grabbing one with crossbones on the top.

Mary Margaret set the tray down on the counter next to him and leaned closer. “I heard you had a bit of a problem picking out Neal’s gift.”

“No, I picked it out just fine,” he said, giving her a smile. “Then I put it in my pocket and walked out without paying. The paying part is what got me.”

She smiled back. “Well, I hope you don’t mind if I tell you it was worth it. Neal loved it!”

“Good.”

“Hey!” David said, walking over with a beer in his hand for Killian. “I don’t want you talking to riff raff like this, Mary Margaret. You know he’s a pirate.”

“You’re not going to let this go for awhile, are you?” he replied.

“Nope,” David said. Mary Margaret gave Killian a sympathetic look and mouthed the word “Sorry” before heading over to some other guests.

“So did you take care of the warrant?” he asked.

“Yea, I just had to write some corporate music hack a check and it’s disappeared,” he explained.  
Luckily, the recording industry got some bad publicity from all the charges they filed against people around the time Killian got his first letter from them in 2002. They were more than happy to ask for a small "donation" to let it go.

“Are we talking about Killian’s arrest?” a voice said from behind them.

Killian turned to see Liam standing there, a smirk on his face.

“There are other things to talk about, you know.”

Liam squinted at him, pretending like he was thinking very hard and coming up with nothing. “I think the only thing to talk about is your arrest,” he said, patting his little brother on the shoulder. “Hey David, did Killian tell you about Emma?”

David’s head turned quickly towards his friends. “Who’s Emma?”

Liam laughed. “Emma is the woman I picked out of the phone book to bail Killian out of jail.”

“Was she hot?”

Killian took a swig from his beer to try and avoid the question, but the warm feeling in his cheeks told him that he probably already answered it for them without saying a word.

“You found him a hot bail bondsman?”

“Bail bondswoman,” Killian interjected.

“All you need to know is that Killian owes me a thank you because she’s hot,” Liam said.

“Whatever," he said quickly before putting the bottle down on the counter. “And on that note, I actually have to go pay my outstanding bill to the bail bondswoman Liam found for me.”

David and Liam both looked at the younger Jones brother with teasing smiles. “Go get ‘em, pirate!” Liam said encouragingly.

Killian rolled his eyes and took one last large swig from his beer bottle. “I’m leaving,” he said with a smile, announcing the obvious.

He stopped to give Mary Margaret a quick hug and thank you before kneeling down to wish Neal a happy birthday. The little boy threw his arms around Killian’s neck, hitting him in the back of the head with Captain Hook’s hook.

“I love my present, Mr. Killian!”

“Oh, good,” he replied before the boy pulled away. “You know, I worked really hard to get that for you so it’s extra special.”

The boy’s already big smile only increased. “Really?” he asked. “That’s so neat!”

“What do you say to Mr. Killian?” Mary Margaret asked.

“Um...thank you!” Neal exclaimed before scampering away to play with his new toy.

Killian smiled and thanked Mary Margaret again before ducking out the door of the Nolans’ apartment. The street wasn’t too busy for a New York sidewalk on a warm spring day so he decided to brave it and take the half hour he needed to walk to Emma’s office. He was hoping the air would get a little cooler though because he felt himself boiling hot in anticipation of seeing her again. He kept playing different scenarios over and over again in his head. What would he say to her when he saw her again? What would they talk about? Would it be weird if he asked her out while also standing in her office to pay off his debt to her?

Of course, he found himself at the door to her building with no idea how to answer any of those. Instead, he simply walked into the lobby, took a deep breath and pressed the button for the elevator.

The doors opened on the ninth floor and Killian headed towards her office, his feet getting heavier with each step. He stopped in front of her door, staring at her name on the front of it in gold letters -- Emma Swan, Bail -- and he raised his hand to knock on the door.

“Can I help you?” interrupted a voice from down the hall back by the elevators.

He turned to see Emma, her blonde hair somewhat disheveled, wearing a red leather jacket over a black t-shirt, skin-tight dark blue jeans, and high-heeled black boots -- well, one high-heeled black boot. She seemed to be holding the heel that was attached to the other one in her hand, causing her to limp in a very undignified way.

“Are you OK?” Killian asked, trying to control the concern in his voice.

“Oh yea, just an occupational hazard,” she replied with a smile. “You’re here to pay your bail?”

“Um, yea,” he stammered.

“Good,” she said. “Thank you for making it so much easier on me than the last guy.”

She unlocked the door and led him into a small one-room office with a desk by the window, a typical high-back leather chair behind it and two uncomfortable-looking wooden chairs in front. The walls were a shade of grey with a bookshelf on one side of the room -- every single one of them seemed to be about some sort of law enforcement or how to catch a criminal. The only thing that looked somewhat personal was a small glass swan paperweight on her desk.

Emma unceremoniously dropped the heel of her shoe on the desk and sat down behind it, motioning for Killian to take a seat as well. Then she started rummaging through a pile of brown manila folders in a box on her desk.

“Remind me what your name was.”

“Um, Killian Jones.”

Her fingers danced over the tabs until she found his and pulled it out. She opened it and began to read, a smile forming on her lips. “I remember you,” she said, looking up at him. “The shoplifting pirate!”

Killian moaned in response. “That’s me,” he said quietly as he pulled a check out of his wallet and handed it to her.

“So did the kid like the pirate gift?”

“Yea,” he replied. “I got that right at least.”

She smiled. “Good.”

Emma grabbed a big red stamp from her desk, placing a large “PAID” mark on the top of the paperwork in his folder. Then she pulled out a large spiral-bound book, marking the payment and writing him a receipt.

“So,” Killian said, trying to break the silence. “Is it just you here?”

“Just me.”

“Seems pretty sparse,” he replied. “Is there a reason you have an office instead of just working from home?”

Emma looked up and gave him a tight smile. “Don’t want the criminals to know where I live,” she replied.

“Oh right, of course,” Killian said before remembering that he, in fact, was one of those criminals. Sort of. Maybe asking her out would be a bad idea. Maybe he should just keep his mouth shut and walk out the door. “So um, now that this is over, would you like to get dinner with me sometime?” _You idiot._

Emma gave him a sympathetic smile. “That’s really sweet, but I don’t date clients,” she said gently.

“Well, now that I’ve paid you, I’m not a client, am I?”

She just continued to smile at him, quickly giving him the idea that this line of questioning was going to be hopeless. It was time for Killian to just pack it up with his dignity still somewhat intact.

“Right then,” he said, pushing himself to his feet before extending a hand towards Emma. “Thank you for your excellent work on my ridiculous case.”

Emma stood and grabbed his hand. “I haven’t forgotten what I said to you that night.”

“What was that?”

“You’re too good looking to be hanging out in a place like this.”

Killian could feel his cheeks getting hot again as he withdrew his hand and stuffed it in his pocket. “Perhaps I’m not the only one,” he replied, taking a breath and quickly avoiding eye contact with the lovely bail bondswoman. “Anyways, um, it was good to see you again?” he asked before clearing his throat. “I mean, it was good to see you again.”

Emma gave him a genuine smile this time. “Yea, you too,” she said, as she walked around from behind her desk. “Here, let me get the door for you.”

She walked past him, giving him a nice view of her ass -- not that he would ever admit to checking it out -- and turned the doorknob.

“Thank you again for being a customer -- and thank your brother as well.”

Killian nodded. “It really was a pleasure meeting you, Emma.”

“Likewise,” she said with a small smile.

With that, she closed the door behind her, leaving Killian alone in the hallway with only his thoughts of how stupid he had been to actually think a woman as beautiful as Emma Swan would agree to go to dinner with him.


	3. Chapter 3

Killian was miserable. He was eating a nice dinner at a nice restaurant with a nice-looking woman, but her personality was awful and it was beginning to piss him off. He must’ve had a few more drinks than he remembered when he asked her for her number at the bar because his date was much more appealing there than at dinner with him tonight.

“So I said to him, ‘Do you really think you can date me with that salary?’ I mean, I was seriously worried we were going to have to do the restaurant’s dishes that night, you know?” The smug woman took another large drink from her second glass of wine. “So advertising. You must be raking in the dough, huh?”

Killian had enough. “Sorry, but can you excuse me for a minute?” he asked. “I just have to go to the men’s room.”

She gave him a smile as he quickly dropped his napkin on the table and headed towards the bathrooms to get a break from this horrendous date. Luckily, he kept his phone in his pocket at all times so he was able to occupy himself in the small hallway leading to the bathrooms by checking the latest links on reddit. Sure, it was a time waster, but it was better than wasting time at the table.

“Um, Killian?”

“Yea,” he replied, casually pulling his eyes away from his phone’s screen to see the most amazing woman standing before him. “Emma!” he said, realizing he had been a little too enthusiastic with his greeting. “It’s good to see you here.”

“Yea,” she replied, a smile creeping onto her face. “I guess it’s better than seeing me in jail again.”

“You have no idea,” Killian said, adding a bit of sarcastic drama to his tone.

Emma just raised her eyebrows at him. “You didn’t get arrested again, did you?”

“No, no, nothing like that. I’m just on a really bad date so, you know, it felt like I was in jail several times so far tonight.”

“Ah,” she replied. “So you’re hiding out by the bathrooms.”

Killian just shrugged his shoulders. “She told me I should take her to a more upscale place next time like the Olive Garden in Times Square, so she really left me no choice.”

“Ouch.”

“So what about you? Bad date?” _Please be a bad date_ , he thought.

“More like wrong date,” she replied. “I called this guy, Mike Johnson, and was going to use our date to lure him out since he owes me money, but I invited the wrong Mike Johnson.”

Killian laughed. “So is the guy you’re having dinner with even a criminal?”

She smiled at his joke, her green eyes shining in the darkly lit hallway. “All I got out of him is that he got a ticket for smoking pot. Oh, and he doesn’t always remember things, so he had to apologize because he couldn’t figure out how we met.”

“Because you just met him tonight.”

“Right,” she said before leaning closer. “But he doesn’t know that.”

Killian smiled and looked back at his phone, trying to play this cool. The last time he saw Emma was a month ago when he dropped off his payment at her office. Despite that, he hadn’t stopped thinking about her and seeing her randomly could make his emotions go very wild if he didn’t take control of them.

And then he had an idea.

“Hey,” he said, trying to sound as casual as possible. “What if you got out of your date by getting me out of mine?”

Emma looked intrigued and turned towards him as she leaned against the wall. “Go on.”

“What if I hadn’t paid you back and you saw me here tonight?” he asked excitedly as he quickly slid his phone in his pocket.

“I would approach you and see if you would like to fix the issue the easy way, which involves me discreetly walking out of here with you, or the hard way, which is not discreet at all.”

He began to get the goofiest grin on his face that he couldn’t control. “How indiscreet? Like ‘We are never going on a second date’ indiscreet?”

Emma’s smile began to match his own. “I could be that indiscreet,” she replied. “Go back to your table and I’ll be there in five minutes.”

If Killian hadn’t had any sort of basic decency or human restraint, he would’ve been down on his knees, worshipping the ground Emma walked on. Instead, he just smiled and squeezed her arm with his hand. “Thank you,” he mouthed quietly to her before heading back to his table.

As he expected, Swan was a woman of her word. He zoned out -- once again -- blocking all the nonsense being spewed by his date. Instead, he watched as Emma returned to her table with her date who, to be honest, was not as attractive as Killian. He watched as Emma made small talk, drank from her wine glass, and then … she saw him. Her face fell in mock shock. She gave her date an apologetic look and said some words to him while she held his hand across the table. Then he looked over at Killian, staring daggers at him, before nodding and giving Emma a tight smile.

The swan started walking, tight green dress hugging all the right curves, hips swaying, high-heeled shoes making a forceful and deliberate clack as she made her way to his table.

Killian ducked his head, staring intently at his pasta so he wouldn’t give anything away.

“Jones?” He looked up to see Emma looking down at him and if he didn’t know this was all fake, he would’ve been truly scared of her presence. “Remember me?”

He looked at his date, who had finally shut up for once to watch what was unfolding at her table. “I’m sorry, I don’t think we’ve met before.”

“Really? Because I think we have.” Emma leaned over the table, giving him an ample view of her cleavage that he was trying very hard not to notice. “I bailed you out of jail for being a shoplifter.”

“A what?” said the squawking voice that belonged to his date.

“Miss, please stay out of this,” Emma instructed. “Now, Jones. Do you want to come with me?”

“I’d rather not,” he said quietly.

“That wasn’t actually a question,” she said harshly. “Stand up, hands behind you.”

All eyes in the restaurant were now on Killian as he gave an exasperated sigh and did as instructed. Emma shoved his face on the table -- he barely missed his plate of pasta -- as she locked his wrists up in handcuffs.

“I’m really sorry,” he said to his date. “Maybe we can go out again and I can make this up to you?”

“That’s really alright,” she replied, dismissing him with a wave of her hand.

Emma yanked him up and started leading him towards the door by her handcuffs. “I’ll call you!” he yelled back at his table.

“Please don’t!” came the reply.

He smiled and focused on the blonde who now had complete control over him as she led him out of the restaurant as patrons stared at their exit. It wasn't until he reached the curb, watching her hail a taxi, that he allowed himself to accept the fact that this plan could succeed.

“I forgot to ask where you live,” Emma said, leaning out into the street with a hand in the air. “I mean, I’m sure it’s in your file, but I don’t remember things like that after I get paid.”

“I’m on the Upper West Side.”

“Good,” she said. “Then you can pay for our cab home since I got you out of that mess.”

“I could do that,” he replied with a smile.

A yellow taxi pulled up next to them and Emma eased him into the backseat -- handcuffs and all -- before sliding in next to him. He looked over her shoulder into the restaurant to see his date at the table he just vacated with none other than Mike Johnson. Apparently, Emma and Killian were going to be involved in a good date night, just not their own.

"Two stops on the Upper West Side," Emma told the cab driver.

Killian noticed the driver do a quick double check of his rearview mirror to confirm the passenger he just picked up did indeed have handcuffs on. He looked over his shoulder to see that Emma had noticed the reaction as well.

“Here, let me get these for you,” she said as she gently unlocked the cuffs on his wrists.

“Thank you again.”

“No problem,” she replied. “And thank you. I couldn’t stand being there any longer talking to that guy.”

He smiled and watched as Emma checked something on her phone.

"So your ban on dating clients..."

"Still in place," she replied without looking up from her phone.

"Right," he said quietly.

There was something special about watching the city pass by a cab window at night, something romantic. Whenever Killian shared a cab with a woman, he liked slipping her hand into his and holding on as the lights and cars and people passed by. But Emma wasn’t any woman and after the quick blow-off she just gave him, he doubted she would be agreeable to him doing the same with her. Instead, he simply rolled down the window a bit, letting the night air hit his face as he tried to gain some control over the whole situation. Unfortunately, the cab was already approaching their neighborhood by the time he finally began to clear his head.

"Hey, can you pull over to that corner?" Emma said to the driver.

"So this is you?" Killian asked as the driver slammed on the brakes.

"Sort of," Emma replies with a mischievous grin. "Remember, don't want my clients knowing where I live."

Killian put his lips together and gave her an awkward smile to once again acknowledge his defeat. He watched as she slid out of the car and was about to close the door when she leaned over and looked at Killian in the backseat.

"Have a good night, Jones," she said sincerely.

"You too."

Emma smiled and slammed the door, leaving Killian to watch her walk away ... again.

"Where to?" the driver asked.

Killian turned to give the driver directions and by the time he looked back, Emma was gone.

"That girl really has ahold of you, doesn't she?" the driver asked from the front seat.

"You have no idea," Killian replied.


	4. Chapter 4

"So you struck out again?" his brother asked teasingly.

“I didn’t strike out,” Killian explained. “She just doesn’t date clients.”

Liam just smiled at him. “If that’s the excuse you want to stick with,” he said before taking another drink of his beer.

Killian wished his brother would have just left things alone instead of asking more questions. After all, the two of them were having a good night. They found an empty table outside on what the bar tried to call a patio but was really a New York City sidewalk with a fake fence around it. It was the perfect summer evening -- still light at 8 o’clock and warm but not too warm. Plus, they both had beers in their hands. It was always nice to have a British beer at a somewhat proper British pub, even if that pub happened to be on the Upper West Side of Manhattan a few blocks from Killian’s apartment.

Of course, it was also a few blocks from Emma’s apartment -- or at least that’s what Killian assumed since he had never actually been there. And judging by his luck with her the past few times he had seen her, he doubted he would ever know what the inside of Emma’s apartment looked like or even really where it was.

“You know you do still owe me a bit of thanks,” Liam said, breaking Killian away from his thoughts of Emma.

“Thanks for what?”

“I could’ve picked any number of bail bondsmen from the internet and I picked Emma just for you,” he said.

Killian scoffed and took another sip of his beer. “Yea, thanks for hooking me up with someone who will never actually hook up with me,” he lamented.

Liam took a deep breath, his tone turning a bit serious. “I really am sorry, brother,” he said. “I shouldn’t tease, I know, especially considering the pull she seems to have on you.”

“It’s OK,” he replied. “It’s not your fault she doesn’t date clients or whatever. I just need to get over it.”

“Cheers to that,” Liam replied, raising his glass as the two brothers clinked them together before drinking some more.

Their fish and chips arrived, which always made them feel a little nostalgic for home. The conversation turned to a new client the advertising firm picked up, then a woman Liam had his eye on. She lived in his building, which Liam thought was a great plan while Killian warned him about dating someone he would run into long after the relationship was over. Unlike his brother, Liam was the type who loved them and left them, which didn’t always work out well despite the fact that he lived in a big city with millions of people.

They were just finishing up their dinner when Killian heard the scream from down the street.

“Stop!” came a woman’s voice as the brothers looked up to see a short bald man barrelling down the sidewalk with a blonde woman chasing after him.

Killian didn’t know why he did what he did next -- perhaps his years in school playing rugby made him miss the good old days. But his instinct was to stand up, jump over the restaurant’s cheap makeshift fence, and help this damsel in distress. The man was running towards him but too worried about the woman pursuing him to watch where he was going. It was the perfect opportunity for Killian to anchor his feet, square his shoulders, and hit the man right in the chest with his elbow. The man went flying back, landing on his ass in the middle of the sidewalk.

“Oi, mate. I believe the lady here told you to stop,” he said in an intimidating voice as he towered over the man.

The woman had finally caught up to them with handcuffs in hand as Liam came over to help her roll the man on his stomach.

“Thanks, Killian,” the woman said as she slapped on the cuffs.

Killian looked over in shock that this woman knew his name. Then he realized why she knew him.

“Emma.”

“Emma?” Liam said from beside his brother.

The blonde pulled her bond skipper up on his feet, her hand holding tight to the man’s arm. “Yea, do I know you?”

“Liam Jones. I called you to bail this one out of jail,” he said, the back of his hand lightly slapping Killian’s shoulder.

Killian gave her a tight smile but kept his mouth shut.

“Oh, yea,” she said. “One of my favorite clients. Unlike this idiot, Killian paid on time.” She pulled the idiot towards the street as the crowd that had gathered parted a bit to let her through. “Sorry I can’t chat, boys. Have to get this guy to jail and all.”

“Right, yea,” Liam replied as he followed her to the curb. “But just one thing. I feel like I have to put a good word in for my brother seeing as how you rejected him -- twice.”

Killian could feel his face flushing with embarrassment. Here he was on the sidewalk after coming to the rescue of this beautiful damsel in distress, and he was about to be humiliated again. This time though, it was going to be in front of his brother and an entire sidewalk full of strangers who had witnessed him tackle some guy because Emma needed his help.

A cab pulled up and Emma quickly opened the door to shove her perp into the back seat. But before getting in, she turned back to the brothers.

"Killian is a great guy and all, but I don’t date clients,” she said matter-of-factly before climbing into the cab and shutting the door.

The crowd around them started to disperse. The brothers, however, stood there staring at the space Emma had just vacated, too stunned to say anything after the entire series of events that had just transpired.

“Man, that is not cool,” said a random stranger in skinny jeans and black Converse. “You caught the guy for her and she burned you.”

Killian turned to the stranger, who just shook his head and walked away.

The brothers slowly walked back to their table with Liam sitting down in his chair while a stunned Killian grabbed the chair he had knocked over when he jumped the fence to take a seat across from his brother again.

“Those are on the house, boys,” their waiter explained as he put two fresh pints down in front of them. "Someone already uploaded photos to Twitter!”

The brothers quietly drank for several minutes as the city buzzed around them. Killian especially needed some time to process all of it since that was by far the most dramatic thing he had been a part of in New York since he got arrested. And of course once again, it had involved a gorgeous blonde who wanted nothing to do with him.

“So that was Emma,” Liam finally said.

“Aye,” Killian replied.

“I can see the appeal,” he said.

Killian stared down at his beer and took a deep breath. “Aye,” he simply replied.

“Listen,” Liam said seriously. “I know I teased you about her and all, but that woman … I highly doubt you will find another one like her in this city.”

Killian gave his brother a sad smile and took another drink of his beer.

“You need to find a way to ask her out again.”

Killian laughed bitterly at the suggestion. “No bloody way! Did you miss the part where she rejected me?”

Liam smiled. “Do it for me?” he asked.

“No.”

“We’ll do baseball rules. You’ve struck out twice so you get one more shot.”

“No.”

Liam leaned back in his seat and gave his brother a look of mock dissatisfaction. “You’ve disappointed me, brother,” he said sarcastically.

Killian couldn’t help but smile back at his teasing brother. “I would rather disappoint you than be disappointed by that woman again.”

“After seeing her in action, that is totally understandable.”


	5. Chapter 5

Killian was like most single people in New York City. If you’re trying to choose between cooking a meal for yourself or going out to grab a slice from the local pizza place, you always default to pizza. He also had the added advantage of living two blocks away from Gray’s Papaya. Just like pizza, hot dogs were a big debate among New Yorkers with most choosing Nathan’s. But then most New Yorkers didn’t live that close to Gray’s.

Frankly, Killian also didn’t want to do much of anything since his shoulder was still a bit tender after hitting a running fugitive in the middle of the sidewalk two days ago. But as soon as Killian started to think about that incident, he quickly decided to push it out of his mind again. He needed to forgot all about Emma Swan -- the sooner, the better.

“What’ll it be?” asked the stout man behind the counter.

“Two chili dogs with a papaya juice.”

“Actually, can you add on a chili dog with cheese?” said a woman behind him.

The clerk simply nodded and gave Killian the total for their meal.

Killian took a deep breath and started digging in his wallet for some cash to distract himself from turning around, knowing exactly who he would see if he did.

“So let me get this straight,” he said without looking up. “You keep turning me down, but you want me to buy you dinner now?”

“I’m paying,” Emma replied. “It’s the least I could do after you tackled my perp for me.”

“Thanks,” Killian said, a bit of bitterness creeping into his voice.

Emma reached around him, her arm brushing his as she handed over money for their dinner. Rather than having some sort of pull on him, her presence just made him angrier. It wasn’t that he wanted to be angry with her but after that last humiliation on the street, he really couldn't take much more of this woman torturing him.

Emma gave him a smile that made his heart beat faster, betraying his decision to not let her have any more control over him. She grabbed a straw for him and some napkins, then picked up their tray of food, giving him a quick nod in the direction of some empty space to stand in front of one of the nearby counters.

Killian was thankful he at least had the two chili dogs to comfort him because the current situation with Emma was odd and unnerving. The woman who rejected him twice just bought him dinner. They both took a bite and Killian gave Emma a slight glance as she picked up a napkin to wipe a little bit of chili off her face. The woman loved chili dogs? Seriously, what else was he going to find attractive in someone so unobtainable?

“So I saw the pictures of you on Twitter,” she finally said casually.

"Oh yea," he replied. "The pub gave Liam and I free beer for a month for that. Best publicity they've ever had."

"Wow," Emma said. "You could pick up a lot of girls with something like that."

Killian just shrugged. "I could," he said quietly before taking another bite.

He'd prefer to use his free beer pass to take a woman he cared about out for a drink and not to pick up random girls at the bar on any given night. But of course, he didn't have a special woman to take with him.

Killian took a drink of his papaya juice -- it really was the perfect match for his chili dog.

"You know I never understood that."

He raised a questioning eyebrow in Emma's direction.

"The papaya juice, I mean," she said.

Killian just pushed his cup closer to her. “Try it,” he said quietly.

She smiled back and grabbed the cup, slowly lifting it to her lips. He could tell by her reaction that she liked it, particularly when she closed her eyes as she pulled the cup away.

“I may have to actually order that next time,” she said, putting the cup back on the counter next to him.

Killian didn’t want to seem eager to take it back, especially after her lips had been on his straw. After her last rejection, he was trying very hard to just let it all be.

An uncomfortable silence fell over them as they ate and watched people walk by. He tried to occupy himself with staring out at the cars and cabs driving past him instead of what was happening right now. Emma must have felt it too -- he glanced over to see her staring at the food in front of her without touching it. But then she turned to him, her green eyes serious but strong.

“Killian, I wanted to thank you for helping me the other day,” she said earnestly.

He just shrugged and looked back out on the street. “It was the right thing to do.”

She touched his forearm, her fingers confidently reaching for his skin. “I mean it,” she said. “I’ve never had anyone help me like that.”

Killian turned and gave her a smile, one he genuinely meant for her.

They quickly finished their food, occasionally making a comment about someone walking by or something going on in the neighborhood. It was definitely nothing deep or serious, just some flippant words to pass the time before they tossed their trash out and left.

As they walked down the sidewalk, Killian could feel the tension slowly leaving him. He decided to just go with all of this rather than fight the urge to put his guard back up knowing how she had rejected him in the past. Instead, the two of them fell into a natural rhythm as they walked and talked, sharing their subway horror stories or commiserating about the lack of air conditioning in their first apartments in the city.

“I was so happy when I could finally afford a window unit,” Emma said. “I parked my ass right in front of that thing for days.”

“I just hung out at my brother’s place and would never leave,” Killian replied. “He finally couldn’t take it anymore and bought one for me so he could have his apartment to himself again.”

Emma laughed as she began to turn down a street off of Broadway. He tried to smile and not look like he felt rejected -- again -- figuring it would be best to part on good terms with her. After all, she had at least made an effort with him tonight and actually bought him dinner.

“So this is you?” he tried to ask casually.

“Yea,” she said, turning back down the street with a slight smile on her face. “You coming?”

Killian hoped his surprise wasn’t obvious, nodding his head casually as he took a few long strides to catch up with her. They continued talking, him asking her how long she had lived on the street and her asking him what he thought was the best place to get a bagel in the neighborhood.

“Bagels By the Park,” he said.

"Definitely," she replied. "Their cream cheese with basil is amazing when you have a hangover."

Killian smiled, knowing exactly what she was talking about. Then he noticed she had stopped walking next to him and turned to see her standing by the steps to a brownstone.

"This is me," she said, motioning to the stoop. "Well, part of it is me. I don't make enough to actually own an entire brownstone."

He laughed. "I wonder if anyone in this city can afford it, because I don't know any of them."

Emma easily smiled at his joke. "So," she said quietly. "I'm glad I ran into you."

"Me too," Killian replied.

He honestly meant it. Despite the rocky start to the night, he ended up having a good time with her. He knew that wasn't going to last, no matter how much he wished it would -- and he wished it would. But if he asked Emma out, he knew that once again her answer was not what he wanted to hear. It would be better for him to just cut his losses and head home.

He nodded towards Emma and put his head down. "So, good night," he said quietly before stepping away from her to head back to his place.

"Wait," she said, grabbing his arm to stop him from leaving. "You aren't going to ask me out?" she said, a smile teasing her lips.

Killian scoffed and stared at his feet. "I don't think I can handle being rejected by you again."

"Who said I would reject you again?"

"Please don't do that, Emma," he said, his eyes looking up at her, pleading with her to stop. "I know your rule about dating clients all too well."

Emma grabbed his hand and stepped closer to him. He would've pulled away from her if she hasn't looked at him with her gorgeous green eyes and smiled.

"After the other night, I think I may have been too dismissive,” she said with a smile teasing her lips. “Now you're more of an apprentice than a client."

Killian took a deep breath. "Do you date apprentices?"

"I might."

Killian moaned. _I shouldn't be doing this_ , he thought to himself before looking into her eyes. "So, uh … would you like to go to dinner with me sometime?"

Emma gave him the biggest smile he had ever seen from her. "I would," she replied. “Um, is Friday OK with you? Say seven o’clock?”

“Yea, that sounds good.”

“OK, so I’ll see you here at 7,” she said. “And you have my number, right?”

Killian smirked. “You mean from my days as a client?” he asked.

Rather than answer, Emma simply gave him one last smile and started walking towards the stairs to her brownstone.

“Good night, Jones,” she said over her shoulder.

“Good night, Swan.”

Killian watched to make sure she got into her place before heading back to his own apartment. He tried desperately to try and stay calm and not look like some grinning idiot. But at that moment on that street in that city, Killian considered himself to be the luckiest bastard around. He pulled his phone out of his pocket to check and see if he had missed any calls or had any messages. The only thing for him was a text from his brother.

“Waited for you at the bar with my free beer, but you ditched me. Better have a good excuse!”

Killian typed back a simple response.

“I’m going on a date with Emma Swan.”


	6. Chapter 6

This was the third shirt he was trying on, but he was having trouble finding something exactly perfect.

"You're being high maintenance," Liam teased as he laid on Killian's bed.

Killian gave him a frustrated look before ripping the shirt off and tossing it on the pile of other rejected options on his floor. Liam just smiled from his spot on the bed, looking at his phone with occasional glances up at his very nervous brother. He had invited himself over to Killian's place to act as moral support, but he didn't seem to be taking the job very seriously.

Killian stood in front his closet again before pulling out a purple and white striped shirt to try on next. This one was a little tighter on him than what he would usually wear, but what he would usually wear was in a heap on the floor.

"I don't know if purple is your color," Liam said.

"Shut up," he replied, buttoning the shirt and tucking it into his charcoal flat-front dress pants. "And get your feet off my sheets already!"

Liam looked over from his phone, raising a patented Jones brother eyebrow to Killian. "Why? Do you think my dirty shoes on your sheets will scare Emma away?"

Killian just rolled his eyes. "I thought you were supposed to be helping me," he said. "You know, giving me support or something."

"You look fine," his brother said, sitting up to give his brother his full attention.

"Just fine?"

"I don't know. I'm not a good judge of these things." Liam took a mockingly frustrated breath and ran his fingers through his hair. "Emma will like it."

"Are you sure?"

"Bloody hell, Killian. Stop overthinking it," he replied, getting up to stand next to his brother. "Just make sure you roll the sleeves up to look a little more casual, and stop with the stuffy buttoning."

Liam always gave Killian a hard time about usually buttoning his shirt up all the way and tonight was obviously not an exception.

"I have to so I can wear a tie," he explained.

"You're not wearing a tie," Liam said, reaching over to unbutton the top three buttons of his shirt. "You're not going somewhere fancy. You're just going to La Cabana."

"Considering the reservation list, it's fancy," he said, walking away from his brother. "I have to get going."

Killian walked into his kitchen, grabbing his wallet, keys and cell phone from a basket on the counter. Then he put on his shoes, making sure they still looked good after he had made a point to polish them up earlier in the day for his date tonight.

"Stay as long as you want, Liam! Just don't be here by the time I get back."

"Why?" he said. "Do you think Ms. Swan may be visiting the place tonight? Is that why it actually looks clean?"

"I'm leaving now," Killian said sarcastically.

"Have a good night," Liam replied earnestly, giving his brother an encouraging smile before he closed the door behind him.

Surprisingly, it wasn't too humid for a summer day in New York, something Killian was extra thankful for as he walked the eight blocks to Emma's apartment. He also was thankful he thought ahead of time about the best way to her place so he could walk by a bodega selling flowers. It may have been a bit too up front for a first date, but he figured it was worth it after all the work he had put in just trying to convince Emma to go out with him.

Luckily, it was easy for him to find her place - something he was a little worried about since it had been dark the last time he had been there. Just as he was about to ring her buzzer, he saw her come out of the door to her apartment. She looked up and could see him through the glass of the front door of the brownstone, a smile immediately spreading across her face as she saw him and the flowers. Instead of locking up her place, she walked over and propped the front door open with her foot.

"Hey!" she said, leaning in to give him a quick peck on the cheek.

"Hi," he replied. "Um, these are for you."

Her smile grew as she reached out to grab the bouquet.

"Wait here one second," she said, immediately turning and walking back into her apartment to drop them off.

Killian watched her walk away for a moment, thankful for the small break so he could calm down a bit and focus on what she was wearing - and what she was wearing was amazing. She went a tad dressier than he did, opting for a sleeveless black dress with a double-ended zipper up the side of it. One end landed on the front of her thigh, which she had left open to show off just a little extra skin, and the other end was zipped down a few inches from the top, allowing the front of it to fold down and give him a beautiful view of her collarbone. Her heels were tall, making her legs look elegant and her ass look stunning.

Emma came back out and locked up behind her this time.

"So I'm in love with these new shoes, but I forgot to see if we were going to be walking far," she said. "How much am I going to regret these?"

"We're only going a few blocks," he explained. "And I hope you don't regret them because you look amazing in them."

She smiled nervously, ducking her head at the compliment and tucking a stray lock of blonde hair behind her ear.

"So where are we eating?" she asked.

"La Cabana," he said. "Just up here on Broadway."

"Oh, the new Mexican place! I've wanted to eat there so badly."

Killian smiled. First the flowers and now the restaurant. He really didn't care anymore about whether he put on the right shirt.

"So how did you get us in there? I wanted to try it with a friend and their first reservation was three weeks away." Emma immediately stopped walking and Killian had to turn to see what had happened to her. "Did you book a reservation three weeks ago?" she asked, shock starting to creep across her face.

"Maybe," he replied teasingly.

"I finally agreed to go out on a date with you two days ago," she said. "I can't decide if you're confident or creepy."

Killian smiled at her. "Neither," he said. "We did the advertising for them so they found a way to squeeze me in."

Emma smiled and started walking next to him again. "I was about to file a restraining order against you or something."

Killian laughed. It was the kind of off-handed joke that a person would only make to someone they were comfortable with, and it was obvious that she had become comfortable with him. Killian's confidence kicked in and he reached out to grab her hand, tucking it into the crook of his elbow as they began to walk again. He took it as a good sign that she didn't find an excuse to pull it away.

The restaurant was packed as expected, but their reservation was waiting, and Killian pulled her chair out first before sitting down himself. He recommended the frozen margarita to her - "The best in town, I promise," he explained. Then the owner of the place stopped by the table to once again thank Killian for the work his agency had done to generate buzz for the new eatery. Killian would have to thank him later for making him look good in front of Emma.

He watched as she took her first drink of her margarita, savoring the initial taste with her eyes closed to emphasize just how much she liked it. Then she opened them to look at him and he realized she caught him.

"You're staring, Jones."

"Sorry," he replied sheepishly, ducking his head to try and avoid her eyes. "You just looked like you were enjoying yourself."

She smiled at him. "Well, I am," she said earnestly. "I don't go out on dates with handsome men all that often, so this is nice."

"Handsome?" he said teasingly. "Well, I aim to please, m'lady."

She smiled and grabbed a chip from the basket that had been put on the table, dipping it in the restaurant's homemade salsa.

"This food is amazing! I can totally understand why they have such a huge wait already," she said, taking another chip from the basket. "So Liam, is he your only brother?"

Killian nodded. "Yea, it's just the two of us. Our mother died when we were younger and our father left a few years after that, so Liam has been both a brother and father to me I guess." He shrugged and gave her a small smile. "It's not bad though. He talked me into going to university in New York after he moved here and I've never looked back."

"So where was home for you?" she asked.

"London," he replied.

Killian and Emma reached for a chip at the same time, their hands awkwardly bumping into each other before he pulled his away, giving her access to the basket. She smiled and quickly grabbed one.

"So, what about you?" Killian asked before reaching for his own. "Do you have any brothers or sisters?"

Emma shook her head. "Nope," she said, her lips pulling into a tight smile. "It was just me."

"I've always wondered what it would've been like to be an only child," he replied. "Like, did you spend alot of time doing adult things with your parents?"

Emma just shook her head and looked down at her drink. "Um, I didn't have any parents either," she explained. "I spent alot of time in the foster system."

"Oh," Killian replied quietly. "Well, now I feel like an ass."

Emma looked up at him and smiled. "It's OK," she said. "I mean frankly, I don't even know why I'm telling you all this. I've never told some of this to men I've been on multiple dates with."

Killian smiled at her confession. He figured the date must be going well if she felt this comfortable with him, at least he hoped so. The conversation was easy, Emma was beautiful, the food was amazing. It was a good first date, although maybe that was because he had needed to work extra hard just to get to this point.

The two of them talked through their entrees, talked through more margaritas, and talked through dessert as well. It was just so nice to be around Emma.

"So Jones," she said, wiping the last of the cinnamon from her churros off on her napkin. "I looked back over your file the other night."

Killian moaned. "Do I dare even ask?"

Emma giggled teasingly at him. "It's not bad," she said. "I just noticed your birthday is next week."

"It is," he replied. "Yea, next week. Liam and I have dinner plans that night if you want to come."

"Um, I'm actually busy both nights next week, chasing down bad guys."

"Both nights?" he asked.

She looked up and gave him the smile that melted his heart. "Right, so your birthday is the day before mine, which is why I brought it up. You know, just something interesting."

Killian smiled at her. "And yet you're saying I can't at least take you out on another date to celebrate it with you."

"Sorry," she replied in a way that made Killian know she really meant it. "The job calls I guess."

"Maybe another time," he said quietly.

"Another time? I don't remember you asking."

Killian looked down and started fiddling with the empty basket on the table. "You wouldn't want to go out with me again, would you?"

Emma grabbed his hand and began running her fingers over the palm of it in such an endearing way that Killian knew her answer before she even said it. He looked up to see her staring at him, her coy smile reaching her eyes.

"I definitely wouldn't mind a second date," she said.

"Good," he replied.

He held on to her hand as they continued to talk, even gesturing for the check and signing his name to the receipt without letting go. And when they were ready to go and she finally released him, his skin still burned with her touch.

The sun had set by the time they finally walked out of the restaurant, Killian not realizing just how much time had passed because he was so transfixed on his lovely dinner companion. As they began to walk back to her place, she immediately stuck her hand through the crook of his elbow - no prompting from him needed this time. She stayed close to him, her leg occasionally brushing his as they stopped to cross the road or turned down a side street before they finally made it to her place.

"So this is me," she said, stopping at the bottom of the stairs leading to her building.

"I remember," Killian said quietly.

She stepped closer to him and gently laid her palm on his chest. "I had an amazing time tonight."

"Me too," he replied, tucking a loose strand of blonde hair behind her ear.

She smiled at his tender touch and then leaned in to kiss him. It initially caught him off guard - he never expected a kiss from someone like Emma Swan on their first date - but he quickly recovered, leaning in to her embrace. Her lips were warm and soft and tasted like strawberry lip gloss. And then all too soon, she pulled away.

"I should get going," she said quietly, her hand still on his chest.

Killian nodded, putting his hand over hers and pulling it away to kiss it gently. It was a bit cheesy and just some stupid thing that he had seen in the movies a million times before, but he looked up to see her beaming at him.

"I'll call you soon?" he asked.

"Yea, I would like that."

Killian nodded as her hand gently slid out of his and she walked up the stairs. He watched as she slipped her key into the lock and then turned around, the light from inside framing her in the doorway in a way that made his heart skip.

"Good night," she said, giving him a small wave before ducking inside.

"Good night," he replied to no one, taking a few moments to stare at her front door before finally walking home.

**Notes for the Chapter:**

> I'm likely going off-canon with that birthday detail. Sorry about that! There's one more chapter left so you only have to hang on a bit longer.


	7. Chapter 7

This was a mistake. He knew it was going to be a mistake. And yet, he couldn't help but do it. The thought of Emma being alone on her birthday and not celebrating it with anyone was just too much for him to think rationally.

Killian put on a white button-down shirt and added his new silver cuff links. They were a birthday gift from his brother the night before and he thought this was the perfect excuse to pull them out and wear them for the first time. He threw on his black pants this time with black ankle boots that he paid way too much for at some fancy European men's shoe store. He walked into the kitchen, grabbing his keys and wallet from his basket, but his cell phone had to stay out a bit longer. He needed to text Emma.

_You get home OK yet?_

_Almost there. It was an easy night tonight. :)_

Killian smiled. At least the timing for his surprise would still be pretty good.

 _Happy birthday, Emma!_  he replied.

_Thanks! Good night, K._

He was definitely hoping it would be a good night. At the very least, she seemed to be in a good mood after nabbing tonight's bail jumper. And he knew her catch from the night before had been a success since she had texted a note telling him that when she wished him happy birthday.

He was about to slide his phone into his pocket when it rang, the caller ID telling him that "Big Brother" was trying to reach him.

"Hello, Liam."

"What's up, little one?"

Killian cringed. "You know I hate when you call me that."

He could hear his brother chuckle on the other end. "So how's your plan coming, brother?"

"I'm leaving now," he replied as he walked towards the door.

"I want to hear all the details."

Killian laughed as he pulled the door closed behind him. "I'm hoping things go well enough that I won't want to tell you all the details."

"Or that you won't have time to call," Liam replied.

"I'm hanging up now."

Killian abruptly pressed the "End call" button and didn't feel bad about it. He knew Liam had good intentions and even encouraged him after he told his brother his plan over dinner last night. But right now, the last thing Killian needed was Liam getting into his head, especially when he was already doubting himself. He didn't need Liam's voice worrying him on top of that.

It was late and the sun had already set by the time Killian made it to the street. Of course, he had checked the closing time for Magnolia Bakery at least five times already today to make sure they would still be open, and he was hoping their cupcake selection hadn't been picked over.

The shop was still brightly lit and still had quite a few choices to pick from. He decided to get four - all different varieties just to make sure he would have at least one that Emma would like. He threw in the usual chocolate and vanilla, then added a red velvet cupcake and a store speciality that the cashier told him tasted just like hot chocolate with whipped cream and cinnamon. It was a little unusual, but he figured it was worth a shot. He also asked if they had candles and matches - it wasn't a necessity, but he thought it would be nice just in case. And sure enough, the woman pulled a few from her stash under the counter. Killian smiled as she packed all of it up and gave him the bag.

Next was a quick stop to the local wine store where he picked up a bottle of white wine for the night. He figured white would be good with cupcakes, and he made sure to get a bottle with a screw cap in case Emma didn't have a corkscrew.

He felt like he had an extra spring in his step as he walked to Emma's place. He had cupcakes and wine for her birthday and was dressed pretty stellar, if he did say so himself. The cufflinks felt like an added sleek touch that gave him an extra boost of confidence.

But as he turned the corner onto Emma's block, his confidence began to falter. Maybe she didn't like surprises. Maybe she didn't like birthdays. She didn't seem too enthusiastic about it when she brought it up on their date last week, but he wasn't sure if that was because she had to do her job or she decided to work that night on purpose. But she did bring it up so maybe she was dropping a hint - or maybe she was just trying to be polite and make conversation.

He finally got to Emma's place and actually stood outside for a few minutes, cupcakes and wine still in his hand, trying to make a final decision about what to do. He took a deep breath and started moving again, walking up the stairs and buzzing her apartment.

The wait felt like an eternity and he watched intently through the front door waiting to see her. The door to her apartment opened and he saw her stick her head out to see him standing there. Her face immediately broke into a smile and her shoulders slumped a bit as the tension she had been holding onto was released. He smiled back and gave her a sort of wave with the wine bottle in his hand. She slowly walked to the door in her bare feet and a short, tight red dress that hugged her body. Once again, she looked stunning.

"Hi," she said quietly, leaning on the doorframe while checking out the man on her front stoop.

"Hi," he replied.

"Is there a reason you're here?"

Killian raised his eyebrow in return, giving back the flirty feeling she was giving off to him. "I just thought I would drop by for a little celebration," he said, his confidence growing. "I figured you couldn't turn me down if I was already on your doorstep."

She gave him a small laugh and ducked her head. "Would you like to come in, pirate?"

His chest warmed when he heard her nickname for him, even if it had been earned by embarrassing means.

"I would like that."

Emma moved out of the doorway to show him in, closing the front door behind him. Then she led him into her apartment, giving him an amazing view of the back of her dress. It was just as jaw dropping from behind, and Killian had to make a mental note to pull himself together so she wouldn't catch him staring at her.

Her apartment was small and modern. She had a living room with bay windows looking out onto the street, a small kitchen, and a door that he assumed led to her bedroom. One wall had a shelf of books against it and there was a small table with two chairs in the space right in front of the windows. She had a worn grey couch in the middle and a TV in the corner. The white walls held only a poster - a picture of a large Germanic castle that looked like something out of a fairy tale. It was sparse and no-nonsense and exactly what he expected from someone like Emma.

"Um, yea," she stammered. "So this is my place."

He looked over at her and smiled. "I like it."

She gave him a nervous smile back before quickly trying to change the subject. "So, what's in the bag?"

"Oh, right. The bag," he replied. "Well, I know you said you don't really celebrate your birthday or whatever, but I thought I would at least stop by with some treats for you."

"Treats?" she asked.

He walked over to her table, took the box out of the bag and placed it on top. "Cupcakes. I don't trust anyone who doesn't like cupcakes. And of course, some wine," he added, placing the bottle on the table.

"I know this sounds a bit crazy, but I actually don't have a corkscrew," she said apologetically.

Killian smiled and reached for the bottle, making a dramatic flourish with his hand as he unscrewed the cap. He was so glad he thought that one out while standing in the wine store as Emma smiled at him in approval and headed for a kitchen cupboard.

"Well, if you already opened the bottle, I guess you can stay for a bit," she said as she pulled two small juice glasses from the cupboard. "I usually just drink beer from a bottle so I don't have any wine glasses."

"I guess I know what to buy you for your birthday next year then," he replied.

Next year? He hoped he hadn't sounded way too presumptuous, but he looked up to see Emma still smiling. Apparently, she either liked what he said or was going to be nice enough to just let it slide. Either way, she didn't call him out on it, choosing to simply let the comment be.

She placed the two glasses on the table while he grabbed the bottle and started pouring.

"So what did you get?" she asked.

He watched her pull the box closer, opening the top carefully to see what's inside. Her smile great wider as she saw the icing on top of the little cakes.

"I went a bit basic since I didn't know exactly what you liked. So there's a chocolate, vanilla, red velvet, and the last one apparently tastes like hot chocolate with cinnamon."

Her eyes immediately snapped to him and he once again began to worry. Did she not like any of them?

"How did you know?" she asked.

"How did I know what?"

She pulled out the hot chocolate cinnamon creation. "One of my favorite things in the world is hot chocolate with cinnamon."

"Really?" Damn, he was feeling good again. "I guess it was just fate then," he said.

Emma sat down at the table with her cupcake and wine as Killian purposely pulled the other chair around so he could sit closer to her. He grabbed the chocolate cupcake and sat down, moving the box out of the way so they could have more room for their food. Emma started to take her wrapper off before Killian remembered what else he brought.

"Wait!" he yelled, startling both of them in the process. "Sorry, I just have one more thing."

He put his hand in the bag and pulled out the candle and matches. As he carefully stuck the candle into Emma's cupcake, he could see an awkward smile forming on her lips. It was as if she was trying to smile to cover up whatever emotion she had bubbling underneath, which made him wonder when the last time was that she had blown one out on her birthday. The match lit easily, as did the candle, and he looked up to see the glow from the flame sparkling in Emma's eyes.

"I'm not going to torture you with my lack of singing ability so just make a wish, Swan," he said quietly.

Emma looked at him and then took a deep breath, easily blowing out the little candle. They both laughed and she gently pulled the waxed stick from her cupcake before peeling off more of the wrapper. Watching her take that first bite was magical, a small moan of delight coming from her mouth as a bit of frosting and cinnamon lingered on her lips.

"This is amazing," she said, licking the sweetness off of her mouth.

Killian smiled and began to dig into his cupcake and had to admit that these were pretty good. He usually tried to avoid Magnolia's because of the line that was out the door, but he now understood why.

"So your bail jumper was easy tonight?" he asked.

"No, but he was an idiot, so it was quicker than I thought it would be," she said.

Killian tried to play it casual by not prying too much, but he couldn't help it. "It wasn't a good date then?"

She smiled at his question. "Dinner with a man who skipped out on the bail that his wife put up for him is never a good date," she said before taking a bite of her cupcake. "You're not jealous, are you, Jones?"

"Jealous? Um…I will admit I am a little jealous," he said, an embarrassed smile creeping on his face. "But in my defense, dinner with a beautiful lady in red is something any man would want."

Emma ducked her head and Killian could see her cheeks begin to turn the same color as her dress. "Thank you," she said quietly before quickly taking a breath and raising her eyes to his again. "But to be fair, I had him cuffed and headed to the station before we even ordered drinks."

He laughed. "Of course you did! I would expect nothing less from Emma Swan."

She let out a small laugh of her own before quickly staring at her wine. And as he took another bite of cupcake, he could feel an awkward silence begin to fill the tiny apartment, not exactly sure of what he had said that made her quiet down so quickly.

"I mean, not that… um… I said something wrong, didn't I?" he stammered.

"No, it's not you. It's just… You know what I wished for?" she asked, staring up at him with her green eyes before quickly giving him an awkward smile and looking back down at the table. "I wished I wouldn't be alone tonight."

Killian felt something tighten in his chest as he tried to control his racing heart. It turned out he hadn't said something bad, he had done something good. Whatever nervousness he had about this plan, whatever he was afraid could go wrong - all of it was gone and replaced with her.

"Well then," he said, clearing his throat to get rid of the shakiness in his voice. "I'm glad I stayed for the cupcakes."

She smiled and fiddled with the edges of her glass. "Me too," she said simply.

Killian reached over to brush a crumb off her cheek, his hand lingering on her warm skin. He could tell she wanted what he wanted as she turned her head, resting it in the palm of his warm hand and closing her eyes. He could feel her melt into his touch, wordlessly encouraging him on.

Killian leaned in, closing the gap between them but stopping just short of her lips. He wanted to make sure this wasn't just some strange moment between them, that she really wanted this too. And she did, pushing herself closer as her lips came in contact with his. They were warm and soft and tasted like cinnamon. He couldn't help himself as he pulled her closer, wrapping his fingers in her long blonde locks, running his hand along the skin on the back of her neck. A jolt of electricity shot through him as he pulled away slightly from Emma, her teeth nibbling gently on his lower lip, causing him to let out an involuntary moan. He gave Emma a nervous smile, one she reciprocated, before he pulled her in again to kiss her longer, harder and more passionately than before.

She finally let go of him and pulled back a bit, giving him the perfect view of her green eyes.

"Wow," she whispered. "I'm glad I finally said yes to that date with you."

"Me too," he quietly said back.

"I guess the third time really was the charm."

Killian smiled. "I guess so," he said, his fingers sliding over her cheek to tuck her messed-up blonde hair back into place. "Happy birthday, Emma Swan."

(The next morning, Killian rolled over in Emma's bed to find her sleeping soundly beside him, his clothes strewn across her floor, and he smiled. Emma had indeed gotten her wish - and he had been more than happy to be the one to give it to her.)

**Notes for the Chapter:**

> So that's it! Thank you all so much for the support with your comments and kudos. You guys are awesome! And I promise I have a few more things that I'm hoping to get posted in the next couple of weeks so here's my blatant plea to have you set up an alert so you know when the next stuff is ready. Thanks again everyone! I hope you liked it!


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